Can Two Players on One Xbox 360 Play Online Together? No

Xbox Live does not support multiple simultaneous accounts on one console for online play.

Why

• License model: Each Gold subscription = one account = one concurrent session.
• Matchmaking: Party system expects 1:1 account:player.
• Anti-cheat / fairness: Prevents "guest" smurfing, boosting.

What Does Work

• Local splitscreen: Many 360 games (Halo, CoD, Gears, Borderlands) support 2–4 players offline / system-link.
• Game Sharing (Home Xbox): Your Gold + digital games shared to one other console. Only one console online at a time per account.
• Separate consoles: Each player needs own 360 + own Gold for simultaneous online.

Xbox One / Series X|S Difference

Modern consoles allow guest sign-in for splitscreen online (host must have Gold; guest plays free). 360 never got this feature.